Love him or hate him, Drake is in the pantheon of the rap game. His catalog is as deep as any all-time great you want to name. He’s one of the most important and transcendent artists for the millennial generation.
He’s been the voice in the speakers of our college parties, our go-to when we’ve gone through heartbreak and everything in between.
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In accordance with the release of his sixth studio album, “Certified Lover Boy,” and after his weekend EP release of “Scary Hours 2,” six of the biggest Drake fans on staff — Jovan Buha, Tim Cato, Will Guillory, Chris Kirschner, Tashan Reed and Jared Weiss — put together our personal top 50 songs. We then combined our lists to form a top 50 ranking of Drake’s songs.
In all, 119 Drake songs received at least one top-50 vote. To keep the pool of songs narrower, we considered only songs Drake was listed as the main artist on. So, for example, “B.B. King Freestyle” on Lil Wayne’s “No Ceilings 3” wasn’t included in this because it’s technically a Wayne song featuring Drake (even though Drizzy destroys the track).
After the initial top-50 cut, we voted again to make sure we were satisfied with the rankings and to give another listen to some songs we might have had second thoughts about.
This is our definitive ranking of Drake’s best songs.
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50. ‘Lemon Pepper Freestyle’
While it’s true that the duo of Drake and Rick Ross never misses, this one’s all about Drizzy. Some of his best work comes when he’s rapping random thoughts over a soulful instrumental with looped vocals and this is the latest example. This was his best lyrical display in a while. — Tashan
49. ‘Controlla’
Over the past half-decade or so, Drake has branched out and experimented with various genres and cultures, taking a particular liking to dancehall and artists like Popcaan. Dancehall Drake isn’t for everyone, but “Controlla” is the peak of that vibe. This song was made to listen to on a beach in the summer.
The Popcaan-assisted version of the song is better than the version that made it onto “Views,” but the song still slaps. If you can listen to this and not get the urge to down a tequila shot — or a spritz, Drake’s favorite — on a desolate Caribbean island (once the pandemic is over, of course), I’m not sure what to tell you. — Jovan
48. ‘Duppy Freestyle’
We all knew this was destined to be a classic from the moment he let out that sarcastic sigh before the opening verse. Drake’s love for throwing subliminal shots at his rivals will be covered throughout this list; it’s one of the staples of his career. But he made no attempt to hide who he was aiming at on this one. Drizzy was fed up with Pusha T’s constant dismissal of his rapping prowess and the complicated relationship he had developed with one of his idols, Kanye West.
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Once he got that sigh off, he proceeded to unleash one of the more impressive lyrical performances of his career, picking apart the motivations and perceived hypocrisy displayed by the two bosses of GOOD Music. Little did Drake know, Pusha’s response to this, “The Story of Adidon,” would be the first time any rapper landed a clean blow on the biggest rapper in the game. — Will
47. ‘Two Birds, One Stone’
This isn’t the best version of a Drake bar session you’ll find, but he floats on this track and covers a couple of relevant topics leading up to the release of “More Life.” The most memorable aspect of this one has to be the shots he sends at Pusha T and Kid Cudi during the latter part of the song, which caused quite a stir.
It was a bold move for Drake, a former child actor, to call King Push a “middle man in this sh*t, boy you was never them guys” in reference to his alleged drug-dealing past. But there was real pushback after bars from Drake seemingly made fun of Kid Cudi’s drug addiction, a jab that was even too much for diehard OVO fans to accept. Either way, this one’s a banger with as much replay value as any Drake loosie. — Will
(Photo by David Wolff – Patrick/Redferns)
46. ‘Worst Behavior’
A central tenet of Drake’s cultural impact is coining phrases that are unmistakably absurd yet unavoidably addictive. I spent most of 2013 yelling “Remember … muthaf*cka?!” to friends, family and strangers on the bus. They would either yell back “Muthaf*ckas never loved us!” or would dial 911. Either one was acceptable.
Credit to DJ Dahi for coming up with a well-layered, glitched-out and chopped-up trap beat that was both abstract as hell yet still on rhythm. If Drake had put more structure into the song and made the first verse more of a verse rather than a drawn-out bridge, this probably could have ranked a lot higher. — Jared
45. ‘0 to 100 / The Catch Up’
Drake sets the tone for this song from the jump: “f*ck bein’ on some chill sh*t.” The stripped-down beat, reminiscent of “Started From The Bottom,” features Drake at his most braggadocious (“If I ain’t the greatest then I’m headed for it”). The instrumental was an immediate classic: BET used it for its cyphers at the 2014 hip-hop Awards, Sprite used it in a commercial with Drake and Nas, and NBA 2K used it in NBA 2K16.
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The most notable line was Drake’s clairvoyant shout-out to Steph Curry, who had yet to become Steph Curry: “This sh*t a muthaf*ckin’ layup/I been Steph Curry with the shot/Been cookin’ with the sauce, Chef Curry with the pot, boy/360 with the wrist, boy.” Steph and Ayesha reciprocated the love with a dance while cooking in their kitchen on her YouTube channel. — Jovan
44. ‘Say What’s Real’
For all the fans of backpack rap who were iffy on Drake early because of his love for melodies and emotional content, this was one of the first songs that made his place among the elite MCs undeniable. He utilized the classic mixtape format of spitting unfiltered bars on another rapper’s beat and added his own unique twist to cover all the bases traditional Drake fans would covet.
Going with the slow, haunting drums featured on Kanye West’s “Say You Will” allowed him to stretch his legs and get off all the thoughts he had stored away in that Blackberry with the side-scroll, hitting every checkmark you’d want from this type of track. He reflects on his rise to stardom and how it’s affected his lifestyle and perception of the people around him. One of the top rap performances of his career. — Will
43. ‘Company’
From the second the ominous beat drops, it’s clear rapper and producer Travis Scott had his hands all over this one. Drake smoothly transitions from melodically rapping to singing as usual as the dark instrumental plays out in the background. The lyricism is nothing special, but it sounds great. The beat switch about halfway through the track and Scott’s crooning feature toward the end takes this song over the top. — Tashan
42. ‘The Motto’
The Motto was a display of Drake’s rising power over popular culture. The hyphy-influenced track was a banger — seriously, it’s probably been too long since you last heard it — that became overshadowed by the acronym it popularized: YOLO (You Only Live Once).
The word took on a life of its own far beyond the song or even Drake. At first, YOLO appeared to be millennials’ cheeky version of carpe diem. But it quickly became played out, from SNL skits, to knockoff merchandise on every street corner, to tattoos, to teenagers’ reckless stunts using the hashtag on social media. Nonetheless, the moment signified that Drake’s co-sign could bring colloquialisms mainstream, something he’s done countless times since. — Jovan
41. ‘From Time’
Right off the jump, we have a beautiful, melancholic piano riff from Chilly Gonzales, who performed the outro of “Marvin’s Room” (we’ll get there a bit later). You know it’s going to be a soulful and introspective song as soon as Jhene Aiko’s vocals come through as she plays the part of an old flame who bluntly tells Drake, “I love me enough for the both of us.”
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Drake admits in his two verses that it’s challenging for him to love, as he’s witnessed his parents’ divorce and his mom, Sandra, tells him she’s almost 70 and still alone. This song also includes the iconic shoutout to Courtney from the Hooters on Peachtree, as Drake professes that she was the one who got away. The song is just classic Drake realizing he’s struggled with countless relationships and not figuring out why it went sideways until it was too late. — Chris
40. Gonzales. Jhene Aiko. Might be my new favorite song. @JheneAiko @chillygonzales @OVO40
— Drizzy (@Drake) August 9, 2013
40. ‘Too Much’
I remember the first time I heard this track, my initial reaction was, “Why does the guy on the hook sound like that?” This was before I was introduced to the genius of Sampha and the soul he brought to one of Drake’s revealing tracks. Unlike most rappers who boast about their place in the game and dream of being the best, Drake goes the opposite direction here. He expresses real anxiety and fear about his ascension, saying it’s increased the pressure he feels daily and negatively affected his relationship with loved ones. And you know anytime we get a few bars about Drake’s mom the song is going to be fire. — Will
39. ‘The Motion’
Drake’s sonic allure has always been more about his careful cultivation and assured delivery, traits that not only masked what he lacked in technical rapping or grandiose singing but also flat-out made it unnecessary. Yet where Drake most effectively resides is in tracks where his lyrics lose any ability to be defined by either verb. “The Motion,” a 2013 loosie released in anticipation of “Nothing Was The Same,” is exactly that.
“I guess that’s just the motion,” Drake slurs during the song’s opening lines, only to drop into melodic cadence while performing the track’s two verses. Today’s music has even blurrier delineations between “sung” and “rapped,” one of the cleanest examples of his influence. But Drake has always been uniquely suited to existing in both spaces at once, a talent never more apparent than on blends like this. — Tim
38. ‘Omerta’
This song may not be as well-known by the masses because it was released as a two-track single to celebrate the Toronto Raptors’ NBA title in 2019. But this is Boastful Drake at his best, stunting on his listeners with lines like, “To me, Benihana is pigeon food” and “I plan to buy your most personal belongings when they up for auction/ Man, truth be told, I think about it often/The petty king.” We all love Drizzy for his introspection, but it’s fun to hear him just stunting on people once in a while. — Will
37. ‘Over’
However you feel about “Thank Me Later” overall as a project, this is classic Drake. He addresses his newfound fame with the opening line — “I know way too many people here right now that I didn’t know last year, who the f*ck are y’all?” — which is crazy to think about given the superstar he’s become. Drake has made better songs and achieved much greater heights since 2010, but here he displays the hunger of a young breakout star yearning to become a legend. He foreshadowed his future successes with the “And this what I’ma do ’til it’s over, ’til it’s over, but it’s far from over” piece of the chorus. It’s safe to say he was right. — Tashan
36. ‘6 P.M. in New York’
Time-stamp Drake is my favorite Drake. Give me a looped beat with four to five minutes of bars any day of the week. From a rapping perspective, this is one of his best performances yet. He hits on his origin story, disses fellow rapper Tyga among others, praises his inner circle and puts his rising confidence on display all on the same track. This was the perfect end to the “If You’re Reading This It’s Too Late” tape, which is quietly one of Drake’s best projects. — Tashan
35. ‘Look What You’ve Done’
This is the most important Drake song for me because I lost my grandmother right when it came out and I was a young mensch who used to drive an Acura, too. I’ve never not cried listening to the voicemail from his grandma at the end, which reminds me so much of my last conversation with my grandmother, which took place just after the album dropped.
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This is the peak of Drake’s songwriting, something truly emotional, vulnerable and yet still with a level of genuine gravitas. It’s basically a spoken-word lounge a capella ballad, with just a beautiful piano progression with some vocal samples looping in the verses before the drums come in for the hook. — Jared
34. ‘Headlines’
Headlines might be Drake’s most underrated hit. The lead single off “Take Care” is Drizzy braggingly acknowledging his newfound status in the rap game as both its present and future. It’s the first time we hear and see his shift toward a tougher outward persona, including talk about catching a body and tucking in his napkin like a mobster. The music video featured several pillars from his brand, which seem familiar a decade later: Toronto landmarks, his OVO crew and head-to-toe Nike clothing. — Jovan
33. ‘Jungle’
The slow, brooding beat of “Jungle” is one of 40’s best productions, which is saying something considering he’s had a hand in almost every Drake song. Add in its soft hook, a sample from Gabriel Garzón Montano, and it makes sense why Drake named his 15-minute cryptic, artsy film (in conjunction with “If You’re Reading This It’s Too Late”) after the track: It’s sonically gorgeous. The one-sided love song is an ode to a girl Drake knew in the “Jungle,” a nickname for Lawrence Heights, a neighborhood in Toronto. — Jovan
(Photo by Andrew Chin/Getty Images)
32. ‘9 A.M. in Dallas’
Drake’s inherent charm has always come from his knowability, never seen more than on his recurring TIME in PLACE series, a comfortable space for Drake to unload his perceived grievances and newest ruminations on life. Released in 2010, “9 A.M. in Dallas” lazily rambles on about women, success, fans asking for the old Drake — an incredible line considering when the track was released — and “Any Given Sunday” references behind a sparse, looping beat. It’s as if a younger Drake is pulling you into an airport lounge at DFW International on a jetlagged morning to tell you everything on his mind.
We’re unlikely to ever get 1 p.m. in the Turks & Caicos, or 2 a.m. in Paris; today’s Drake is too guarded to record such a record again. But you always have a soft spot for someone whose friendship simply drifted away, and you can always go back and remember the times you shared. And whatever you think about Drake, it’s unquestionable that he was always willing to share what his life was like with you. — Tim
31. ‘Uptown’
“Bun and Wayne and Drake in here, man, this gon’ be a great night.” — Bun B, 2009
That quote succinctly sums up this song. All three floated on this Boi-1da produced track, who sampled “Uptown Girl” by Billy Joel and turned it into one of the most fire beats on “So Far Gone.” We also get auto-tuned Weezy at the top of his game fresh off of the release of “Tha Carter III,” which is undoubtedly one of the greatest rap albums of this millennium. — Chris
30. ‘Trust Issues’
This is a deep cut for Drake stans, since it was a loosie and got overshadowed by “Marvin’s Room.” The bridge is the original hook for “I’m on One” off the DJ Khaled album that came in spring 2011, when this was also released. “I’m on One” became one of the biggest singles of the decade for good reason, but this song is the epitome of breakout-era, Drake back when he was making “Take Care” and was doing a lot of dark, soulful work with 40 on production.
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This was one of the few songs where Drake’s singing is actually kinda good, and while the beat is pretty spacious and warm, there is this haunting guitar riff in the middle of the hook that really brings it all together. When he switches up and comes in with the flow halfway through the track, it pushed this song into classic Drake territory. — Jared
29. ‘Free Spirit’
While “Trust Issues” was the prototype for a Drake R&B song, “Free Spirit” is the ultimate rap version of this side of Drake. This is some of 40’s best work, flipping a Sade sample into another warm, atmospheric beat with a distant guitar riff piercing through the middle like a meteor entering the earth’s atmosphere. This was probably going to be the centerpiece of “YOLO,” the Drake-Ross mixtape that never saw the light of day, and the world is a worse place for it.
The fact that the hook of this song is telling a lover to get his name tattooed to prove their love is just the kind of absurdity that Drake and Rick Ross somehow make seem plausible. Plus, Ross is perfectly ostentatious with his verse. The first two bars are some of the best of his career and are just way too graphic to be printed here. This was in my top five, and I’m just disappointed it fell so far in our rankings. — Jared
28. ‘The Calm’
I’ll never understand why this song doesn’t get more praise. The muffled beat doesn’t do much, but Drake raps at an elite level. He alludes to the contradictory emotions that come with his creative process: “I’m just in my zone. I call this sh*t the calm. Yeah, but I’m the furthest thing from calm.” The lyrics may come across as arrogant, but as he explains: “What they viewing as bragging is the way that I maintain. The sh*t I write while staring out the window of a plane is the single-handed reason I remain … me.” Drake is introspective, clever, honest and open, which were all common themes that helped his audience develop a genuine connection throughout his classic “So Far Gone” tape. — Tashan
27. ‘Legend’
It’s pretty clear I have a type, and that’s Drake spitting over ’90s slow-jam samples. This time it was “So Anxious” by Ginuwine, the song I used to sing to my crush in fifth grade before I really understood what any of the lyrics actually meant. I loved how PartyNextDoor uses the Ginuwine sample first as an ambient synth bed, then brings the actual coherent vocal sample over that as a staccato squeak of what I assume was the sound of an impact driver at his local auto mechanic comes in from the edges.
This was the opener to “If You’re Reading This it’s Too Late,” which has become Drake’s cult classic. So to open it up saying “Oh my god, if I die, I’m a legend” is the kind of humility you would expect from Aubrey. — Jared
26. ‘Forever’
How many times has Drake’s objectively corny line “First name ever, last name greatest” been yelled out in high school locker rooms and basketball blacktops? You recognize “Forever” the moment the very first air horn screeches the song into existence, and the Boi-1da track hardly stops for a breath as it cycles through verses from Drake, Kanye West, Lil Wayne and Eminem. It’s almost unbelievable these four titans — Drake, back then, just the talented kid brother to those three — would congregate on a single track, but it makes more sense when you realize LeBron James was the one who orchestrated it for the soundtrack of his “More than a Game” documentary. The song, for all its uncomfortable lines and the terrible hashtag rap trend it began, still feels like the defining track for a moment in sound. — Tim
(Photo by Jesse D. Garrabrant/NBAE via Getty Images)
25. ‘Successful’
This song is wild to listen to in 2021. Over a decade has passed since the release, which was Drake’s second single after “Best I Ever Had.” In the song, Drake raps about how he wants money, cars and clothes because that’s how he views success. He didn’t know it at the time, but a few years after this dropped in 2009, Drake would be at the top of the rap game and a megastar who transcended the word “success.” This song is the anthem for those who grind hard for what they want to achieve in life.
This song is also unintentionally funny because Trey Songz is on this song about being successful and years later, Drake raps on “From Time” how a woman once told him how he’d never be as big as Trey Songz — “Boy, was she wrong.” — Chris
24. ‘Over My Dead Body’
It’s possible, in 2021, to imagine the most-hyped new rapper releasing an anticipated debut album that starts with a delicate piano beat and haunting female vocals telling an unknown lover “I’m doing OK.” In 2011, though, “Over My Dead Body” was an instant declaration that Drake planned to sledgehammer what a hip-hop release could be. “Take Care,” as we know now, progresses through rich, gorgeous melodies and sounds interspersed with harder percussion raps and beats on its way to critical acclaim. But think about the first time you played this album front to back, and how foreign these first few seconds must’ve been. How many must have thought they’d fallen for a bait-and-switch on some illegal download site. Only for Drake to float over the beat moments later, saying, “I think I killed e’rybody in the game last year, man, f— it, I was on, though.”
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What influence Drake exerted onto the genre in the decade to come stemmed directly from this unexpected duality: a rapper who sings, a wealthy braggadocio who admits the showy lifestyle doesn’t necessarily make him happy, a womanizer who’s vulnerable enough to admit he misses ones who’ve gotten away, an artist who can blend hip-hop and pop into some unmistakable amalgamation of the two. While “Over My Dead Body” was never meant to loop on radio stations or be screamed at concerts, it connects Drake’s two sides as well as any other song on this album — and sets you up for the rest that is to come. — Tim
23. ‘Jodeci Freestyle’
“IRS all in my books, getting they Matlock on. All this capital, it’s like I left the caps-lock on.”
Drake gets a lot of heat for not being a good rapper or needing a ghostwriter to deliver bars. Those people must’ve not listened to this song when it dropped, and it’s a shame that most people probably didn’t hear this until Drake packaged his loosies under one project — “Care Package” — in 2019, because this is one of his hardest songs. J. Cole, who’s featured on the track, murders his verse, and his story of how his verse came together is wild. I’m biased because Drake and Cole are two of my favorite rappers in the game, but they need to collab more because they bring out the best in each other in this song and on Cole’s “In The Morning.” — Chris
22. ‘The Real Her’
Lil Wayne, Andre 3000 and Drake all on the same record, what else needs to be said? This wasn’t one of the hits from “Take Care” that you’d hear on the radio, but it’s undoubtedly one of the best songs on the album and one of the best songs of Drake’s discography, period. It’s romantically emotional in a way that some may call soft, but Drake is an R&B artist on this track, not a rapper trying to be hard. Wayne and 3000’s guest verses remain on topic but add some tempo to prevent the lengthy song from getting monotonous. — Tashan
21. ‘Days In The East’
I think I single-handedly dragged this song this high, which I’m proud of. It’s my favorite Drake loosie, with the late-night booty call elevating into a cross-continent flight across a slow, haunting beat. Rumors swirled that this song is about Rihanna, with whom Drake had been on and off for years when this released (2014). He even samples a line from Rihanna’s hit “Stay.” That transitions into the best part of the song, the third verse, post-beat switch, when Drake raps about having tea at Erykah Badu’s house and refers to himself in third-person as “The Boy” 15 times. — Jovan
20. ‘The Ride’
Drake takes us through a detailed look at the good and bad of becoming a superstar, and how difficult it is for him to relate to anyone who isn’t in his shoes. But it’s not just the glitz and glamor of doing dinners at French Laundry in Napa Valley. He covers the grind he went through to get there and how much he’s looking forward to what’s next. Add that to hypnotic background vocals provided by The Weeknd on a simple but effective beat and you get a classic Drake B-Side. — Will
19. ‘Fear’
This is one of Drake’s best and most forgotten songs because it wasn’t a single and instead is the finale of the seven-song EP “So Far Gone.” Drake’s creative genius shines in the final line of the third verse as he alludes to how money changed everything for him, and the first line on his debut album “Thank Me Later” starts with the line “Money just changed everything” on “Fireworks.” (As an aside, I’m pissed as hell “Fireworks” didn’t make the cut because it’s one of my top 10 Drake songs because the lyricism is unreal and raw.)
“Fear” is an unfiltered look into Drake’s mind as he shares his anxieties as he goes from a popular Toronto mixtape rapper to full-fledged rap star who’s about to embark on his journey to being one of the greatest rappers of all time. — Chris
18. ‘Club Paradise’
When Drake raps “And this’ll be the year that I won’t even feel s—” midway through the final verse, he sounds like he’s trying to convince himself. “Club Paradise” is a sprawling look back at the old life Drake had in Toronto and the new one that’s replacing it, one where former friends doubt his sincerity and tell him, “You don’t know this city anymore.” But Drake, while at times longing for what once was and surprised even old flames have moved on, ultimately isn’t reassured by the new luxuries he brags about.
What comforts him throughout this track is what’s still with him even in this new life: his mother, his childhood friend Chubbs, and his favorite Toronto establishment Club Paradise, a place where, no matter how much he changes, he still knows the strippers by their real names. — Tim
17. ‘Dreams Money Can Buy’
Whether you see Drake as a culture vulture or a legitimate advocate for new musical talent, it’s stunning how many unexpected places his name has appeared for features or endorsem*nts throughout the past decade. Yet the most bewildering still might be his first notable example, 2011’s “Dreams Money Can Buy,” a song that samples heavily from Jai Paul’s “BTSTU.”
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Paul is one of modern music’s most regrettable stories, a British electronic artist which appeared out of nowhere with two of the most genre-bending tracks that set a course for much of the modern R&B you hear today. In 2013, an unfinished album was leaked online, after which Paul disappeared for more than six years until a 2019 reemergence featuring two new tracks and an explanation of how his incomplete art being stolen from him caused him to feel jaded. It’s a fascinating story, albeit not related whatsoever to the 2011 Drake release featured here. But Drake has never failed to find new sounds to complement his latest ruminations on wealth, women and the world, and he does so with stunning effectiveness here with a massive assist from the mysterious British artist. — Tim
16. ‘Cameras/Good Ones Go’
One of the specialties of Drake and 40 is taking a fire sample and remaking it better, with Drake’s voice vastly improving the sound of any beat. “On Cameras/Good Ones Go,” the dynamic duo samples Jon B.’s “Calling On You,” with Drake disparaging the role that photos and media can play in creating the perception of a relationship. Later, he pleads with an old flame to not move on and marry, claiming he’ll be ready for her soon.
The opening lines of the song — “Word on road is the clique about to blow” — spawned Drake’s unofficially official fan social account, WordOnRd, which replaced its predecessor, AllThingsFresh.net (ATF). The Weeknd’s influence on the song is clear, especially during “Good Ones Go,” when the beat slows and intensifies as we can hear him crooning his ad-libs. — Jovan
15. ‘Passionfruit’
I never knew how to define my aesthetic until I read this.
Put "Passionfruit" On Repeat And Watch "Passengers" With No Sound. Then You Will Understand Me.
— Jaden (@jaden) March 19, 2017
Good to know that my unique sense of self is apparently completely unoriginal, but Drake and British producer Nana Rogues captured it perfectly. From Rogues’ space flute to the house bass line, this was the lovely softer side of Drake’s London sound on “More Life.” It all coalesces to create this feeling of floating on clouds, looking around you to see waves crashing to the shore in paradise. The lyrics are simple, but Drake delivers them with a reserved passion. It culminated in his best pop hit and proof that even if he is a culture vulture, he does it better than anyone. — Jared
14. ‘Do Not Disturb’
I’ll let you guys behind the curtain on this one: When we originally put this list together, we had to completely redo some of the rankings because we forgot to give this song the respect it deserves. I mean, it’s easy to forget about this one given the way it’s ducked off as the final track on “More Life” behind all those Caribbean dance tracks. I’ll admit I had to revisit it to remind myself how much Drake went crazy on this Boi-1da-produced instrumental with the sick Snoh Aalegra sample in the background.
This is another example of Drake emptying his notebook to reveal his current state after mixed reviews for his previous album, “Views,” along with his struggles to enjoy the fruits of his labor because life is moving so fast. Drake is always at his best when he gets in his reflective bag. — Will
13. ‘Best I Ever Had’
The first time I heard this song, I was leaving my high school campus, blasting Power 106 (if you know, you know). I missed them announcing the song and thought it was some new rap/R&B duo. After the song ended, the DJ said, “That was that new heat, ‘Best I Ever Had,’ from Drake.” Drake? Who’s that? When I got home, I looked him up, illegally downloaded “So Far Gone” and immediately became the biggest Drake stan I know (I’ll take on any challenger).
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If you were playing someone Drake’s discography for the first time, I think this is the best place to start. It was his first breakout hit, cracking the No. 2 spot on Billboard, his highest mark until “One Dance” went No. 1 in 2016. The song features a more primitive version of what makes Drake special: the ability to seamlessly transition from crooning a catchy hook into a rap verse, while combining being braggadocious (“Buzz so big I could probably sell a blank disc”), vulnerable (“Baby, you my everything, you all I ever wanted”) and charming with the right amount of corny (“You could have my heart or we could share it like the last slice”).
The Kanye West-directed music video missed the mark, with some even suggesting West tried to sabotage Drake — a claim ahead of its time. While some artists around the 2008-09 range would have faded after a hit this big, Drake used it as a launching pad to become the biggest rap star of the 2010s. — Jovan
12. ‘Chicago Freestyle’
This was by far my most-listened-to song in 2020. It’s the perfect song to listen to when you just want to drive around the city with nowhere to go and reflect. Some people might think it’s recency bias to have a song from this past year rated this highly with his catalog being as deep as it is, but from the start with GIVĒON on the chorus to sampling Eminem’s “Superman” to Drake pouring out what he’s learned in the past decade with his relationships, it’s Drizzy at his best. While this song wasn’t part of his “A.M./P.M.” time-stamp grouping that are all bangers, this song essentially could be titled “2:30 A.M. in Chicago” and it would work. — Chris
(Photo by Andrew Chin/Getty Images)
11. ‘Furthest Thing’
Somewhere between psychotic and iconic
Somewhere between I want it and I got it
Somewhere between I’m sober and I’m lifted
Somewhere between a mistress and commitment
The opening bars of “Furthest Thing,” like much of Drake’s early discography, are about his quest for self-discovery. Drake fesses up to some of the recent mistakes weighing on him, including breaking promises to people in his life as he deals with the problems of fame and success, and leading on multiple women when he had no intention of remaining faithful to them. “The furthest thing from perfect, like everyone I know,” he sings. There is a dichotomy to the song, with the melancholy balanced by upbeat boasting, particularly in the second half when the beat changes and Drake gets in his rap bag. — Jovan
10. ‘5 A.M. in Toronto’
“Give these n—– the look, the verse and even the hook, that’s why every song sound like Drake featuring Drake.” That may be Drake’s greatest line ever. This song is just incredible. The beat bangs and Drake is spitting. This, along with the rest of the time-stamp Drake collection, is what I point to when people foolishly attempt to argue that Drake isn’t one of the best rappers ever. — Tashan
9. ‘Girls Love Beyoncé’
This song most obviously starts with Drake and 40 managing to pull off one of the smoothest covers of the 21st century with their rendition of Destiny’s Child’s “Say My Name,” but more importantly, it helped introduce the hip-hop world to one of the most important unsung heroes of modern pop music: James Fauntleroy. Fauntleroy manages to cover the “Say My Name” hook with a reworked cadence and beautiful layering that somehow makes it seem fresh. 40 brilliantly takes some heavily layered clips of Fauntleroy vocalizing and washes them over until they turn into essentially a synth bed.
But this is the ultimate Drake R&B groove, almost an antithesis to “Marvin’s Room” in its smooth beat, forward delivery and storyline. Rather than Drake staring at his camera roll with a tear in his eye on the roof deck of the W Hollywood, this is Drake picking out which fur coat to wear before heading to a dinner party at Nobu with Chris Boucher, Aaliyah’s ghost, Jeff Koons, Zoe Kravitz and Bernard Arnault.
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This is the song that plays in the montage of Drake driving to that party in the music video, cutting to a scene of everyone toasting with Dom Pérignon as he stares longingly at a couple on their third date laughing in the opposite corner of the restaurant. When Beyoncé said “Say My Name” 21 years ago, she just wanted her man to be straight-up with her, whether he was cheating with that girl who works at Circuit City or not. In 2013, Drake is just looking for someone he can leave through the front door with and not worry about her catching feelings when photos of him with (insert IG model here) show up every other week. — Jared
8. ‘4 P.M. in Calabasas’
Time-stamp Drake has been a recurring theme throughout this list. It’s him saying to the listener before they even click on the track, “Yeah, I’m about to go in on this one.” But “4 P.M. in Calabasas” is different. It isn’t just Drake laying out some of his best bars on a fire beat. This track may have been when Drake’s arrogance as an artist reached an all-time high.
We’ve covered his love for poking fun at his peers with subliminal bars, but he took it much further with this one. He openly mocks legendary rap figure Puffy Combs (and maybe Joe Budden?) for the entirety of this track by masterfully bobbing and weaving through different flows and dropping some of Diddy’s classic lines like, “And we can’t stop” or “Make you dance to this.” The root of the issue between Puff and Drake is still unclear, but it certainly drew a different kind of motivation from someone who usually saves this kind of vitriol for members of GOOD Music.
Drake’s constant dilemma during his rise to the top is perfectly encapsulated in his line “The higher I get, the less they accept me. Even had the OGs tryna press me.” He’s lamented in the past how much he has yearned for a higher level of respect from the gods of the rap game based on his accomplishments, and this was one of the few times he let it be known that he’d had enough. This is easily one of the most underrated diss songs of all time. — Will
7. ‘Paris Morton Music’
This song should be played at one volume only: full blast. I don’t care if it’s on your phone, your Bluetooth speaker or your car speakers with the windows down — they must be down.
You might recognize the beat from Rick Ross’ “Aston Martin Music,” another song you must blast at full volume and risk blowing your speakers on. Drake was actually sent this beat first from Rook of J.U.S.T.I.C.E. League, but Ross ended up having a full song with Drake just singing the chorus.
Then Drake did his own version of “Aston Martin Music” and bodied the beat. This is, personally, my favorite flow from start to finish from Drake. It’s simply a masterpiece. — Chris
(Photo by Ron Turenne/NBAE via Getty Images)
6. ‘Lord Knows’
Where do I begin? The sample of Andrew Brown and National Baptist Convention Choir’s gospel song “Lord, Lord” that’s weaved in throughout the entire track is insane. Drake goes off.
He’s clearly aware of what he’s become with lyrics like “I changed rap forever.” While this song is far removed from his R&B and pop cuts, he takes time to discredit the detractors of his “softer” lanes: “I’m hearing all of the jokes, I know that they tryna push me. I know that showing emotion don’t ever mean I’m a puss*.”
Drake is talking his smack, which is when he’s at his best as a rapper. Rick Ross drops in with ad-libs and ends things with one of his best feature verses ever. This is the best song that “Take Care,” which is a classic, has to offer. Period. — Tashan
5. ‘Tuscan Leather’
The rapturous critical reception and unadulterated popularity of 2011’s “Take Care” permanently changed Drake. Gone was whatever remained of his rapper-turned-actor persona, an oh-look-how-cute-he-is span of his musical career where it was still conceivable Drake might just be a flavor or a fad. What stood in its place was rap’s new headliner. Just three years after his first mixtape crept online, Drake had evolved into the genre’s trendsetter, its tastemaker. On “Tuscan Leather,” the opening song to his first full release since his hip-hop coronation, Drake loudly proclaims: I know.
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“Tuscan Leather” booms with the assured confidence of an artist who knows where he now falls in the hierarchy. “Comin’ off the last record, I’m gettin’ 20 million off the record,” he raps in the opening line. The track marches onward for six minutes while Noah “40” Shebib flips a Whitney Houston sample three times, not even pausing for a hook. Why bother? “This is nothin’ for the radio,” he says, “but they’ll still play it though.” It’s that new Drizzy Drake, after all. That’s just the way it goes.
What “Tuscan Leather” represents is a tour de force beginning for Drake’s finest hour. It’s the opening soulful salvo from a 59-minute parade acknowledging his rise to the top, and then building on it, promising that this new Drake isn’t content to sit around leaving voicemails and wallowing in the recorded vulnerability that first brought him attention. No, he knows he now holds the crown, and he’s making sure you know it, too. — Tim
4. ‘HYFR’
When we started these rankings, I put this in at No. 1 in Sharpie. It’s the bangiest of bangers, a simple but brilliant hook from Drizzy and Weezy over masterful production from T-Minus. He took a guitar riff from a Paula Abdul track and turned it into a post-apocalyptic synthwave melody over a DJ Screw sample. Drake comes in rapping at double time like he’s Bun B after a few gallons of Red Bull, and this track is just littered with classic bars and an unforgettable hook.
From Drake opening it with a story about how his exes get their tuition paid, to “I learned Hennessy and enemies is one hell of a mixture,” “They say love is in the air, so I hold my breath until my face turn purple,” “We eat each other whenever we at the dinner table,” I could go on. Also, the Director X music video of Drake having the baddest bar mitzvah of all time just adds to the legend. This was the peak of Drake tapping into his H-Town identity, the place where he first flew in 2008 to meet Weezy and launch his career. — Jared
3. ‘Back to Back’
The genesis of one of the best diss tracks of this generation is Meek Mill got mad that people were comparing the two rappers. Meek tweeted how Drake doesn’t write his own songs, so there’s no reason he should be in the same stratosphere as him in the rap pantheon.
Eight days later, Drake dropped a bomb on Meek’s head and destroyed him in under three minutes. It was the second of two diss tracks — “Charged Up” being the other directed Meek’s way.
In “Back to Back,” Drake took aim at Meek’s relationship with Nicki Minaj and dissed him for being an opening act on her “The Pinkprint” Tour by rapping, “Is that a world tour or your girl’s tour” and then following up by saying, “I know that you gotta be a thug for her/this ain’t what she meant when she told you to open up more,” which was a direct response to Nicki’s song “Buy a Heart,” in which she expresses doubts over Meek’s emotions.
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And then, the missile connects when Drake says, “Trigger fingers turn to Twitter fingers,” which takes Meek’s opening line in “In God We Trust” where he boasts about his trigger fingers but they’re now being used to moan online over someone’s rapping ability. He concludes by letting Meek know how he’s currently being torched by someone who occasionally sings instead of raps.
It’s a murderous tune that made Meek a punchline for months afterward and put to sleep anyone still doubting whether Drizzy can rap with the best of them. Drake performed the song at OVO Fest with a bunch of fan-created memes, which was comedy. — Chris
(Photo by George Pimentel/Getty Images)
2. ‘Pound Cake/Paris Morton Music 2’
I’m probably biased because Drake and Jay-Z are my two favorite rappers of all time, but this is one of my favorite songs of all time. Jimmy Smith’s “Jimmy Smith Rap” is sampled for the intro, which transitions into a mix of looped vocals from Ellie Goulding’s “Don’t Say a Word” and a sample of Wu-Tang Clan’s “C.R.E.A.M.” Drake doesn’t say a word for the first 1:04, but when he appears at 1:05 with “Yeah,” you already know something amazing is coming.
Drake is on a track with the greatest rapper of all time, so he comes correct early: “Overly focused, it’s far from the time to rest now. Debates growin’ ’bout who they think is the best now. Took a while, got the jokers out of the deck now. I’m holdin’ all the cards and n—– wanna play chess now.” After Jay-Z’s verse, there’s a beat switch that marks the end of “Pound Cake” and the beginning of “Paris Morton Music 2.”
It’s no coincidence that Drake ramps his aggression up to another tier following Jay-Z and boldly states how he’s passed him. Keep in mind, this song was released in 2013 and Aubrey Drake Graham already felt that way. Whether or not you agree, you have to respect it. Drake ends the song with the line, “Nothing was the same, dog.” Eight years later, ahead of the release of his sixth studio album, it’s hard to argue with him. — Tashan
1. ‘Marvin’s Room’
This isn’t the song with the best beat, the most extravagant production, the best bars or the most Instagrammable lyrics for captions. “Marvin’s Room” is a song with minimal production, which is the point, because Drake is spilling his heart out and is as raw as we’ve seen any rapper be over a track with such commercial success as this one had as the smash hit off his best album, “Take Care.”
Drake is raw and revealing as he stupidly calls an ex while he’s drunk and tells her how her man sucks and will never be as good as him and she probably still thinks about the time they shared together. Meanwhile, Drake is likely drunk and alone in a candlelit bathtub as he listens to Boyz II Men’s “End of the Road” on repeat.
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“Marvin’s Room” is the quintessential Drake song. It’s about another failed relationship, likely by his own doing, and he gets into his feelings over the loss. The song is so relatable to everyone who has experienced heartbreak, then watched their ex get into another relationship. Who among us hasn’t creeped on the IG of a woman or man you’ve either dated or gone on dates with and questioned that person’s thinking? Drake just eloquently brings that real-life tale over a haunting and mesmerizing track for the world to view who he has portrayed himself to be deep down for well over a decade now: an emotionally fragile person who wants to be loved but fails to reciprocate to the women who enter his life. — Chris
(Top photo: Getty; Vaughn Ridley, Jason Koerner, Christie Goodwin, Kevin Mazur)
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